WO2013018752A3 - グリセリンの脱水反応によるアクロレイン及びアクリル酸の製造用触媒と、その製造法 - Google Patents

グリセリンの脱水反応によるアクロレイン及びアクリル酸の製造用触媒と、その製造法 Download PDF

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Publication number
WO2013018752A3
WO2013018752A3 PCT/JP2012/069305 JP2012069305W WO2013018752A3 WO 2013018752 A3 WO2013018752 A3 WO 2013018752A3 JP 2012069305 W JP2012069305 W JP 2012069305W WO 2013018752 A3 WO2013018752 A3 WO 2013018752A3
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Prior art keywords
glycerin
catalyst
metal oxide
acrylic acid
dehydration
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Application number
PCT/JP2012/069305
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English (en)
French (fr)
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WO2013018752A2 (ja
Inventor
公人 奥村
康志 小林
良太 平岡
ジャン－ルク デュブワ
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日本化薬株式会社
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Application filed by 日本化薬株式会社 filed Critical 日本化薬株式会社
Priority to US14/235,460 priority Critical patent/US20140206527A1/en
Priority to EP12819876.9A priority patent/EP2737943A2/en
Priority to KR1020147004332A priority patent/KR20140053209A/ko
Priority to BR112014001873A priority patent/BR112014001873A2/pt
Priority to CN201280038313.5A priority patent/CN103717306A/zh
Publication of WO2013018752A2 publication Critical patent/WO2013018752A2/ja
Publication of WO2013018752A3 publication Critical patent/WO2013018752A3/ja

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24—Chromium, molybdenum or tungsten
    • B01J23/30—Tungsten
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/63—Pore volume
    • B01J35/633—Pore volume less than 0.5 ml/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/66—Pore distribution
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/08—Heat treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C47/22—Acryaldehyde; Methacryaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

　本発明は、グリセリンを脱水反応させて高収率で不飽和アルデヒド及び不飽和カルボン酸を製造することができ、かつグリセリン転化率、不飽和アルデヒド及び不飽和カルボン酸の収率の経時低下の少ないグリセリン脱水反応触媒を提供することにある。　本発明は、特に、グリセリンを脱水反応させて高収率かつ高寿命でアクロレイン及びアクリル酸を製造することができるグリセリン脱水反応触媒を提供することにある。　更に、本発明は、そのような触媒の製造法を提供することを目的とする。　ＴｉＯ2、ＳｉＯ2、Ａｌ2Ｏ3、ＺｒＯ2およびＮｂ2Ｏ5から選択される少なくとも一種の金属酸化物を含み、かつ２ｎｍより大きく５０ｎｍ未満の範囲内にあるメソ細孔の細孔容積に対する５０ｎｍ以上のマクロ孔の細孔容積の比が０．５以上である二元細孔を有する担体に、Ｗ含有金属酸化物を担持した、またはＷ含有金属酸化物に加え、Ｐ、Ｓｉ、ＭｏおよびＶの中から選択される少なくとも１種の元素含有金属酸化物を担持した、グリセリンを接触脱水反応してアクロレイン及びアクリル酸を製造するのに用いるグリセリン脱水用の触媒。
PCT/JP2012/069305 2011-07-29 2012-07-30 グリセリンの脱水反応によるアクロレイン及びアクリル酸の製造用触媒と、その製造法 WO2013018752A2 (ja)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US14/235,460 US20140206527A1 (en) 2011-07-29 2012-07-30 Catalyst For Preparing Acrolein And Acrylic Acid By Dehydration Of Glycerin, And Its Production Process
EP12819876.9A EP2737943A2 (en) 2011-07-29 2012-07-30 Catalyst for manufacture of acrolein and acrylic acid by means of dehydration of glycerin, and manufacturing method for same
KR1020147004332A KR20140053209A (ko) 2011-07-29 2012-07-30 글리세린의 탈수 반응에 의한 아크롤레인 및 아크릴산의 제조용 촉매와, 그의 제조법
BR112014001873A BR112014001873A2 (pt) 2011-07-29 2012-07-30 catalisador para preparação de acroleína e ácido acrílico por desidratação de glicerina, e seu processo de produção
CN201280038313.5A CN103717306A (zh) 2011-07-29 2012-07-30 用于通过甘油的脱水反应制造丙烯醛和丙烯酸的催化剂及其制造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-167366 2011-07-29
JP2011167366 2011-07-29

Publications (2)

Publication Number Publication Date
WO2013018752A2 WO2013018752A2 (ja) 2013-02-07
WO2013018752A3 true WO2013018752A3 (ja) 2013-03-21

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PCT/JP2012/069305 WO2013018752A2 (ja) 2011-07-29 2012-07-30 グリセリンの脱水反応によるアクロレイン及びアクリル酸の製造用触媒と、その製造法

Country Status (7)

Country Link
US (1) US20140206527A1 (ja)
EP (1) EP2737943A2 (ja)
JP (1) JPWO2013018752A1 (ja)
KR (1) KR20140053209A (ja)
CN (1) CN103717306A (ja)
BR (1) BR112014001873A2 (ja)
WO (1) WO2013018752A2 (ja)

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WO2013017904A1 (en) * 2011-07-29 2013-02-07 Arkema France Improved process of dehydration reactions
CN103717306A (zh) * 2011-07-29 2014-04-09 日本化药株式会社 用于通过甘油的脱水反应制造丙烯醛和丙烯酸的催化剂及其制造方法
KR101616528B1 (ko) * 2013-07-16 2016-04-28 주식회사 엘지화학 글리세린 탈수반응용 촉매, 이의 제조 방법 및 아크롤레인의 제조 방법
JP2015058391A (ja) * 2013-09-18 2015-03-30 日本化薬株式会社 グリセリンの脱水反応によるアクロレイン及びアクリル酸の製造用触媒
KR101671436B1 (ko) 2014-12-11 2016-11-01 한국과학기술연구원 글리세롤 탈수반응용 니오븀계 촉매 조성물
KR101657987B1 (ko) 2015-05-11 2016-09-21 한국과학기술연구원 글리세롤 탈수반응용 니오븀계 무정형 촉매 및 이의 제조방법
KR102052708B1 (ko) 2015-12-22 2019-12-09 주식회사 엘지화학 글리세린 탈수 반응용 촉매, 이의 제조 방법 및 상기 촉매를 이용한 아크롤레인의 제조 방법
US11104575B2 (en) * 2016-05-12 2021-08-31 Fujian Institute Of Research On The Structure Of Matter, Chinese Academy Of Science Nanocatalysts, preparation methods and applications for reforming carbon dioxide and methane to syngas
CN109305899B (zh) * 2017-07-28 2021-09-03 中国石油化工股份有限公司 甘油脱水生产丙烯醛的方法
CN109304164B (zh) * 2017-07-28 2021-08-03 中国石油化工股份有限公司 甘油一步法合成丙烯酸催化剂
JP2020179312A (ja) * 2019-04-23 2020-11-05 日本化薬株式会社 触媒及びその製造方法
AT522938B1 (de) * 2019-08-27 2021-06-15 OMV Downstream GmbH Katalysator
CN113083309B (zh) * 2021-04-09 2022-01-28 北京化工大学 一种高效催化甘油氧化制备甘油酸的催化剂、其制备方法及用途
CN114405493A (zh) * 2021-12-20 2022-04-29 西安凯立新材料股份有限公司 一种高强度大孔径氧化铝-氧化钛复合载体的制备方法
CN115709060B (zh) * 2022-11-11 2024-03-29 浙江工业大学 一种用于甘油制烯丙醇的催化剂及其制备方法

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JP2012157794A (ja) * 2011-01-29 2012-08-23 Hokkaido Univ グリセリン脱水用触媒、その製造方法並びに該触媒を用いたアクロレインの製造方法

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BR112014001873A2 (pt) 2017-02-21
KR20140053209A (ko) 2014-05-07
JPWO2013018752A1 (ja) 2015-03-05
CN103717306A (zh) 2014-04-09
EP2737943A2 (en) 2014-06-04
US20140206527A1 (en) 2014-07-24
WO2013018752A2 (ja) 2013-02-07

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